Here’s How to Spend a Relaxing Weekend in Rhinebeck

The historic town of Rhinebeck packs boutique shopping, gourmet eats, and cultural to-dos into just a few square blocks in Dutchess County.

Long before cities like Beacon and Hudson lured New York City weekenders and out-of-towners, Rhinebeck served as the go-to Hudson Valley retreat. These days, the Dutchess County spot is as charming as ever, with its abundance of boutique shops, manicured sidewalks, and on-trend restaurants.

Regardless of whether you visit on the regular or have never stepped foot into town before, make this the season you take advantage of all that Rhinebeck has to offer. Try our guide first, then make your own when you plan a return trip — which you will.

9:30 a.m. – Start the day on a sweet note at Samuel’s Sweet Shop

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Every day, without fail, locals and visitors alike flock to Samuel’s Sweet Shop for coffee, candy, and confections. The spot serves hot or cold coffee to balance out the sugar-centric menu. Pair your caffeine with a fresh apple turnover, muffin, or any other pastry on offer that morning. And did we mention the shop is celebrity-owned? Stop in on the right morning for the chance to run into Paul Rudd, Jeffrey Dean Morgan, or Hilarie Burton. If you happen to pick up a bit of candy while you’re there, we don’t blame you.

42 East Market St, Rhinebeck

10:30 a.m. – Explore Wilderstein Historic Site

Located in the heart of the Hudson Valley, Wilderstein Historic Site charms with its Queen Anne-style design and expansive grounds. On select dates throughout the year, visitors can tour the mansion and explore the vintage treasures that the Suckley family amassed during their three generations inside the house. Outside, 40 acres of manicured gardens and grasses call to hikers and walkers.

330 Morton Rd, Rhinebeck

12 p.m. – Eat farm-to-table with a twist at The Amsterdam

The Amsterdam brings European flavor to Hudson Valley cuisine in the heart of Rhinebeck. Open for brunch, lunch, and dinner on select days during the week, The Amsterdam delights with tapas-style bites like cheese boards, steak tartare, and house-made ricotta. For brunch, indulge in biscuits and gravy, croque monsieur, shakshuka, or a chorizo burrito for something with more spice.

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6380 Mill St, Rhinebeck

1:30 p.m. – Fly high at the Old Rhinebeck Aerodrome


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If you visit Rhinebeck over the weekend, don’t leave without making a trip to the Aerodrome on a Saturday or Sunday afternoon. That’s when the airshows, the high-flying spectacles with historic planes and skilled pilots, take place from June 15 through October 20. Biplane rides are available both before and after the shows, and the museum is open daily from May through October.

9 Norton Rd, Red Hook

4 p.m. – Shop and stroll along Market and Mill


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When it comes to shopping, Rhinebeck is a dream destination. With quaint boutiques lining the picturesque Market and Mill Streets, it is all too easy to lose track of time as you hop from one storefront to the next.  For a truly unique experience, head to Merriweather’s, Periwinkles, or Oblong Books & Music. They’re the perfect places to find a one-of-a-kind gift or the knickknack you never knew you needed.

If clothing is more your vibe, don’t skip out on a visit to Workers & Dreamers for chic sweaters and accessories or Winter Sun & Summer Moon for colorful bits and bobs.

6:30 p.m. – Dine in style at Terrapin

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Terrapin is a required stop on any successful trip to Rhinebeck. For a more casual meal, head to the Red Bistro, where you can munch on Hudson Valley Cattle Company hamburgers, barbecue duck quesadillas, and uncle Vinny’s special rigatoni. On fancier occasions, make a reservation for the Dining Room, where you can savor the likes of gingered leek and tofu pot stickers, New York strip steak, pumpkin ravioli, and seasonal desserts.

6426 Montgomery St, Rhinebeck

6:30 p.m. – Or grab dinner and a drink at {pretty to think so}

If you crave a spot with a serious vibe and intimate aesthetic, look no further than {pretty to think so}, an eatery that’s just as well-known for its innovative cocktails as it is for its elegant menu. Get the evening started with drinks like Never Fully Dressed, a pour that features vodka, pink vermouth, absinthe verte, and Creole bitters. From there, sample and share dishes from the fresh-as-can-be raw bar or dig into bites like stuffed delicata squash and blue oyster risotto.

6417 Montgomery St, Rhinebeck

8 p.m. – Get a drink and a history lesson at The Tavern at The Beekman Arms


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Instead of letting its historical origins fall to the wayside, the historic inn embraces them wholeheartedly. The 1766 Dutchess County building is the oldest inn in America that charms with an Americana aesthetic that includes an open hearth fireplace and a picturesque bar. Take it all in over a cheeky cocktail or Hudson Valley beer. Of course, the food is divine, too, in case you’re still feeling like a snack after dinner ends.

6387 Mill St, Rhinebeck

9 p.m. – Call it a night at Mirbeau Inn & Spa Rhinebeck

Mirbeau is a true Hudson Valley gem that has been recognized by the Forbes Travel Guide, which gave it a four-star rating for 2024. Spend your evening in the spa for massage therapies, facials, body treatments, and more. As for the rooms, they’re the ultimate in local luxury, thanks to thoughtful touches like cozy fireplaces, spacious bathrooms with oversized French-style soaking tubs, and some of the most luscious beds we’ve ever seen.

46 West Market St, Rhinebeck

Related: What to Eat and Where to Go for a Perfect Day in Red Hook

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